Detail of "13173-09-6"

Reference

Enzyme-controlled reactions giving alkanols of use in the synthesis of biologically active molecules

Enzyme-controlled reactions giving alkanols of use in the synthesis of biologically active molecules. Roberts, Stanley M. (Dep. Chem. Res., Glaxo Group Res., Greenford/Middlesex UB6 0HE, UK). Ciba Found. Symp., 111(Enzymes Org. Synth.), 31-9 (English) 1985. CODEN: CIBSB4. ISSN: 0300-5208. DOCUMENT TYPE: Journal CA Section: 16 (Fermentation and Bioindustrial Chemistry) Section cross-reference(s): 2, 63 (±)-Bicyclo[3.2.0]hept-2-en-6-one (I) [62182-73-4] was reduced with a variety of fungi including yeasts. Bakers' yeast gave 6-exo-(1R,5S,6S)-bicyclo[3.2.0]hept-2-en-6-ol (II) [65914-53-6] and 6-endo-(1S,5R,6S)-bicyclo[3.2.0]hept-2-en-6-ol (III) [62990-19-6], whereas Curvularia lunata and Mortierella ramanniana gave only III and optically active bicycloheptenone. The optically active bicycloheptenols were used to prep. prostaglandin F2a in the natural configuration.

Use of microorganisms for the resolution of synthetically useful bicyclo[3

Use of microorganisms for the resolution of synthetically useful bicyclo[3.2.0]hept-2-en-6-ones. Roberts, Stanley M. (Dep. Microbiol. Chem., Glaxo Group Res. Ltd., Middlesex UB6 0HE, UK). NATO ASI Ser., Ser. C, 178(Enzymes Catal. Org. Synth.), 55-75 (English) 1986. CODEN: NSCSDW. DOCUMENT TYPE: Journal CA Section: 16 (Fermentation and Bioindustrial Chemistry) The resoln. of synthetically useful, racemic cyclobutanone derivs. using whole-cell systems was investigated. Bicyclo[3.2.0]hept-2-en-6-one (I) [13173-09-6] was reduced using actively fermenting bakers' yeast to give the corresponding 6-endo-ol [62182-74-5] and 6-exo-ol [88082-90-0]. In both cases the S-configuration was prevalent at the newly created chiral center. The same bicyclic ketone was converted into optically active 6S-6-endo-ol [62990-19-6] and enantiomerically enriched starting material using Mortierella ramanniana. The alcs. and optically active ketone produced in this way were efficiently converted into naturally occurring prostaglandins F2a [551-11-1] and A2 [13345-50-1]. 7,7-Dimethylbicyclo[3.2.0]hept-2-en-6-one [100853-05-2] was transformed by M. ramanniana into 6(S)-7,7-dimethylbicyclohepten-6-endo-ol [65941-79-9] and 6(S)-7,7-dimethylbicyclohepten-6-exo-ol [107437-57-0] with excellent enantioselectivity. The former optically active alc. was converted into the pheromone (+)-eldanolide [84107-93-7] and both alcs. were converted into the arachidonic acid metabolite (+-leukotriene B4 [71160-24-2]. Thus, microorganisms can be used to resolve bicyclo[3. 107338-36-3 is just another one chemical used in this study.2.0]heptenones, enhancing the usefulness of these compds. for the synthesis of a variety of chiral natural products. .